There is a leadership pattern I’ve seen at nearly every non-startup company I’ve worked at: the organization decides it needs to be excellent at something it is currently not excellent at. A new platform. A new GTM play. A transformation with a capital T. Yet the plan, the entire plan, can be boiled down to …
Author Archives: Wil Schobeiri
Why Dates are Hard
A few months ago, I wrote a post about organizational biases to ship frequently vs plan heavily. This post attempts to be a tangible follow-up on the concepts laid out there. I recently decided to build a piece of custom furniture for my living room, a table to house a collection of music equipment, with …
Eleven Ways The Ground Beneath Software Development Has Shifted
In the ~25 years I’ve been writing software, I’ve never been so excited (and terrified!) by what is happening in technology. It seems like we’re living through a watershed moment. Not one that’s coming: one that has actually already occurred, with most of the industry still grappling to understand the implications. And that’s for one …
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The NIH Tax: How “Not Invented Here” Quietly Kills Your Margin and Your Roadmap
In NIH-heavy orgs, “build” isn’t a decision. It’s a reflex. Engineers don’t evaluate buy/partner/build. They default to build—either because they assume nothing good exists, or because they quietly discount the true internal costs until the spreadsheet says what they want it to say. Sometimes that reflex produces real advantage. Most of the time, it produces …
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Plan Heavy vs Ship Light
Paul Graham once wrote about startups being default alive or default dead — a brutally simple way to check whether a company’s current trajectory leads to survival or collapse. I like the concept of defaults: what are the organizational tendencies that arise as a result of the cultural revealed preferences? One such dichotomy is the …
Act Your Size
One of the great paradoxes in tech is how early or mid-stage startups try to cosplay as late-stage enterprises long before they have any of the fundamentals that justify it. The temptation to scale prematurely is natural: looking “big” feels like progress! It feels safe. It feels like you’re doing it right. But: acting big …
Obvious Rules to Live By, for Corporate Sanity
After nearly two decades of corporate experience spanning seed stage startup to Fortune 500, I’ve slowly built a list of rules to live by at work. They’re pretty obvious, but that’s ok – most good ideas are. I’d like to think they help keep work more straightforward, less wasteful, and probably a lot more pleasant. …
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TCF: The Origin Story
Over the last few years, as the IAB Europe’s Transparency and Consent Framework (TCF) has been in and out of the news, a few of my friends across the industry have nudged me to put the story behind the TCF down on paper. After eight years, some of the details are a bit hazy to …
Deliverables vs. Outcomes: A Classic Corporate Tragedy
Technology teams often confuse “done” with “delivered,” neglecting impact. Focusing on deliverables over outcomes leads to dysfunction, cynicism, and lower quality products…
On Building Resilience in a Startup
If the word “resilience” makes you groan, much like the words “synergy,” “best-in-class” or “unprecedented times” might, I get it. But, hear me out. Resilience is one of the most underappreciated and important character traits in humans—especially when working at a startup. So what does it mean to be resilient within a startup context? Embrace …